Pyridine oxide compound, and process for producing...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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08034947

ABSTRACT:
The invention relates to a pyridine oxide compound represented by formula (I), an optically active compound thereof, a salt thereof and a hydrate thereof, and, in the presence of the compound as a catalyst, performing 1) a method for producing an ester compound or an amide compound from a carboxylic acid equivalent and an alcohol or an amine, 2) an asymmetric esterification reaction or 3) an asymmetric amidation reaction. In formula (I), each R1may be the same as the other R1or different and each R1represents an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom, a sulfur atom or a nitrogen atom; each R2may be the same as the other R2or different and each R2represents a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom or the like, and R3and R4may be the same or different and R3and R4each represent a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a carboxyl group, an ester group, a cyano group, a halogen atom, an oxygen atom or the like.

REFERENCES:
patent: 07-133283 (1995-05-01), None
patent: 2003-335731 (2003-11-01), None
Vippagunta et al., “Crystalline Solid”, Advanced Drug Delivery Reviews 48 (2001) 3-26.
Guillory (in Brittain ed.), “Polymorphism, etc.,” NY: Marcel Dekker, Inc., 1999, 1-2, 183-226.
Nakajima, Makoto et al., Enantioselective Michael additions of β-keto esters to a, β-unsaturated carbonyl compounds catalyzed by a chiral biquinoline N,N′-dioxide-scandium trifluoromethanesulfonate complex, Tetrahedron, Sep. 8, 2003, vol. 59, No. 37, p. 7307-7313.
Regnouf, de Vains, J. B. et al., New symmetric and unsymmetric polyfunctionalized 2,2′-bipyridines, Journal of Heterocyclic Chemistry, 1994, vol. 31, No. 4, p. 1069-77, see compound 12.
Sano, T. And Oriyama, T., “Development of catalytic asymmetric acylation of alcohols in the presence of a chiral 1, 2-diamine”, Journal of Synthetic Organic Chemistry, 1999, 57 (7), pp. 598-607.
Shina, Isamu et al. “A New Condensation Reaction for the Synthesis of the Carboxylic Esters from Nearly Equimolar Amounts of Carboxylic Acids and Alcohols Using 2-Methyl-6-nitrobenzoic Anhydride” Chemistry Letters, Mar. 5, 2002, No. 3, pp. 286-287.
Written Opinion, PCT/JP2006/302830.

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